Today on BILLIONS, I'm sitting down with Larry Aschebrook, the guy who invented a market that Wall Street didn't think existed.

Larry started personally buying shares in Twitter and Uber on the side and he realized: there are thousands of employees sitting on life-changing paper gains, with zero liquidity, waiting for companies that might never IPO.

So in 2011, he quit his safe university job and launched G Squared, a fund to solve that problem. Nobody took him seriously. The secondary market was "taboo." Companies thought selling shares meant you were failing.Today, he manages $5 billion.

He turned a $150M Spotify bet into $1 billion. He made $800M on Coursera. And the market he built is now worth $140 billion a year.

Larry, welcome to BILLIONS.TIMELINE :

00:00 : The psychology of the secondary market pioneer.

01:13 : Quitting a decade-long career for a "ghost" market.

03:23 : The Hustle: Cold-calling alumni for early Twitter and Uber shares.

05:41 : The $150 million Spotify bet and the $9M personal risk with zero collateral.

11:19 : Data Arbitrage: How Larry knew record labels were secretly buying Spotify.

15:43 : Scaling G Squared: From a $35 million pool to $7 billion AUM.

20:05 : Why DPI (Cash Back) is the only metric that matters, and why paper gains are a lie.

25:09 : The Scars: Learning from the "quick commerce" collapse and other losses.

37:09 : The Future: OpenAI, SpaceX, and the evolution of private liquidity.

53:12 : Advice for Founders: Why you must hire "grinders," not just pedigree.

REFERENCES :

• Daniel Ek 

• Spencer McLeod

• Mitchell Green

• Jim Simons

• Elon Musk 

• Spotify 

• Twitter 

• Uber 

• Palantir 

• Coursera 

• Anthropic 

• OpenAI 

• SpaceX 

• Stripe 

• Wiz 

• Toast 

• Netflix

• Apple Music 

• Instacart 

• Postmates 

• Meituan 

• Alibaba 

• Turo 

• Getaround

• Klarna 

• Revolut 

• Databricks 

• 23andMe 

• Gorillas 

• Pagaya⁠